Reaction #586080

Reaction equation

octadecylamine

di(propylene glycol) dimethyl ether

sodium acetate

cyanuric chloride

→

N,N′,N″-trioctadecyl-1,3,5-triazine-2,4,6-triamine

Solvents

acetic acid

2-Propanol

Conditions

Workup

1. 1
   Temperatureto reflux out of the reaction mixture
2. 2
   TemperatureThe reaction mixture was heated to 170° C. for sixteen hours
3. 3
   Temperaturehad cooled to 80° C
4. 4
   FiltrationThe precipitate was filtered at room temperature
5. 5
   Washwashed with excess 2-propanol
6. 6
   workup.STIRRINGThe solid was stirred
7. 7
   Temperaturein refluxing water (2.00 liters) for two hours
8. 8
   Filtrationfiltered
9. 9
   Washwashed with excess water
10. 10
    workup.STIRRINGThe solid was stirred
11. 11
    Temperaturein refluxing 2-propanol (2.00 liters)
12. 12
    Filtrationfiltered
13. 13
    Washwashed with excess 2-propanol

Procedure

Under a nitrogen atmosphere, a mixture of octadecylamine (389 grams, 1.44 mol), di(propylene glycol) dimethyl ether (1.50 liters), sodium acetate (134 grams, 1.63 mol), and cyanuric chloride (88.4 grams, 0.479 mol) was stirred for thirty minutes and then heated to 85° C. for two hours. The reaction mixture was heated to 155° C. at which temperature acetic acid was allowed to reflux out of the reaction mixture. The reaction mixture was heated to 170° C. for sixteen hours. 2-Propanol (1.60 liters) was added to the reaction mixture when it had cooled to 80° C. The precipitate was filtered at room temperature and washed with excess 2-propanol. The solid was stirred in refluxing water (2.00 liters) for two hours, filtered, and washed with excess water. The solid was stirred in refluxing 2-propanol (2.00 liters), filtered, and washed with excess 2-propanol to yield 377 grams of N,N′,N″-trioctadecyl-1,3,5-triazine-2,4,6-triamine as a white solid.

Source